Surprising Relationship Evolutions Ch. 02

Connor sat across the table from his co-worker and "friend with benefits" Bobbie at their favorite Mexican restaurant. He was a bit nervous, which he displayed by being only slightly less confident than normal.

He felt like a perv. But he was enjoying the hell out of it. But why?

Connor was a military veteran, who now used his skills in a stateside job he did not talk about. Could not, really. Bobbie was not included, or excluded, so to speak, because she was in the same office, doing the same job. They found themselves partnering on capers more and more. In more ways than one.

They had been doing the horizontal bop for months now. It had begun shortly after Connor caught his wife Kathleen in bed with another man, and had left her.

Bobbie was his best friend. She knew all of his deep, dark secrets. She had encouraged him to seek counseling to deal with his wife's infidelity, and in the process found out about much more.

Well, she knew almost everything. She knew his sexual proclivities and the why. She knew he liked to be denied. She knew he had fantasies about female led relationships. She knew he had been considering chastity play.

What she didn't know was that he had pulled the trigger on that fantasy. He was wearing a high-tech, high-dollar chastity device as they ate. He needed a key holder and had chosen one.

And it was not her.

She dipped a chip into the queso, accidentally breaking the chip he already had there. "Oops, sorry..."

He smiled, "No biggie."

His demeanor was only slightly off. But for Bobbie he may as well have been waiving a semaphore flag.

"Alright, what's up? Spill."

He should have known she could read his tells.

"Well, you know about my fantasies, right?"

Trying to lead into it slowly. No use.

Bobbie's eyes lit up. She dropped the sandal from her right foot and raised her bare foot under the table before he could continue. Her toes squeezed around the hard metal of the stainless steel tube rather than the pliant phallus she was accustomed to feeling.

"You dirty little pervert! You went and did it, didn't you?"

Their relationship was such that he knew there was no malice in her comment. She was taunting him, knowing that the subtle humiliation would arouse the hell out of him. His cock tried in vain to become erect.

He groaned. She laughed, knowing what she had done.

She was not necessarily into male orgasm denial or chastity. But for him, she had become quite practiced at denying him, and had grown accustomed to taking her pleasure without always returning the favor. She would readily get into chastity play also. They had discussed it frequently. Besides, being selfish in bed had become very rewarding.

Bobbie had made it very clear there was no room in her life for a permanent relationship. "No hearth and home" as she put it. But she did love Connor. She enjoyed their time together and would always be faithful to him... as a friend. Even if he were to someday find someone else and marry again. It just doesn't get better than that.

She held out her hand. "Keys."

He bowed his head.

Now her temper flared. "You gave the keys to your cunt ex-wife??? What the fuck, dude?!"

Other patrons looked over at them.

It had been Bobbie who suggested he get counseling. She had encouraged him to sleep with his ex when the therapist suggested it... for closure if nothing else. She had even been open to his remarrying Kathleen, if that was what he wanted. But deep inside, she didn't trust the cheating whore.

He quickly and vehemently asserted, "Oh, hell no. Of course not."

She calmed as quickly as she had flared. Which was a quality he greatly appreciated. Now she was just puzzled. To her knowledge, he was only fucking her, and his ex.

"Alrightly then. Um, who?"

She was going to think he was insane.

"Vivian."

He was always telling people his female partner was smarter than he was. He had puzzled over who to give the keys to his penile freedom to for quite some time. She got it immediately.

"Fucking brilliant!"

She actually high-fived him. "A disinterested third party who knows all about your umm... needs. And this way me and Big-Dick Barbie can't screw with each other by holding onto the keys. Good boy, you little fucker."

Bobbie had all kinds of disparaging pet names for his ex. Big-Dick Barbie was because when Connor had caught her, she was being fucked senseless by the biggest cock he had ever seen.

"But I have to ask. What am I supposed to do when I want dick now? Ask our therapist for permission? Go elsewhere?"

He paused before eating another chip. "I don't know, she wouldn't tell me. Said she wants to talk to you and Kathleen about it. And, I suppose I can't object if you go elsewhere. It wouldn't even technically be cuckolding. Just sharing, I suppose."

Bobbie did not take offense at his relaxed attitude about her potentially bedding someone else. Neither had any hold on the other.

However.

"I think I'll see this through for a bit. I ain't gonna spread my legs for just anybody. And in case you hadn't noticed, I'm kinda particular with you."

They had already discussed his reasons for being interested in chastity, but now she asked him how it actually felt. He explained how the cage felt like a firm, almost comforting grip on his cock when it tried to grow. Also, how knowing he could not so much as masturbate if he wanted, he was on a continuous sexual high. Even the thought of sexual contact was exceedingly arousing. He didn't know how he would handle the extreme high of making love to her knowing he could not have her, even if he did not want to deny himself.

She grinned. "This sounds fun. Only one way to find out. Take me back to my place, I am gonna wear your ass out."

When they got back to her place, he instinctively wanted to take care of her needs. She stopped him.

"Uh-uh. Stand still. Obey. Good boy."

She very slowly removed his work clothes, as if she were unwrapping a gift with great anticipation. First sliding his belt and holster off. Then lifting his polo shirt over his head.

She tenderly traced his muscular chest, shoulders and arms with just her fingertips. She traced the scars he had accumulated over the years on his chest, abdomen, and his back. Some of them were deep scratch marks she had put there.

Her feminine touch and her apparent fascination aroused him, and his cock was already desperately attempting to expand within its prison.

Bobbie unfastened his khaki cargo pants and let them drop to his ankles, the items in his pockets weighing them down enough that no assistance was needed from her.

She knelt down on her knees before him, and removed his shoes and socks. She coaxed him to left his feet so she could remove the pants.

Now all that was left to expose him completely were his blue boxers. She again caressed him, his calves, his thighs, more battle scars.

She did not want to have to pull the boxers down and delay the excitement of the finale. So she drew her knife from HER cargo pants, snicked the waistband of his boxers, then returned the knife. With suddenness, she used both hands to rip his boxers apart, discarding the ruined underwear without looking at it so she could remain focused on his crotch.

"Damn. What have you gotten yourself into, little boy?"

She traced the small, downward pointing shiny metal phallus which somehow, unreasonably, had to encase his much bigger shaft. She inspected the locking assembly, remarking on its effectiveness, twisting the tiny padlock. She made his pirouette so she could inspect the leather belt around his waist and under his buttocks, secured to the cage, which made his slipping the portable prison off impossible without a key.

She traced and hefted his very full, exposed testicles, and then squeezed them until he groaned. She noted that he groaned, but still did not complain.

Bobbie looked into his eyes and made a great display of fellating the small, barely 2 inch long tube. He groaned again when she forced her tongue through the vents and the small slit which allowed him to urinate, or as she noticed, seep pre-cum.

"Hmm. Not nearly as satisfying as taking your beautiful cock in my mouth. I cannot believe all of that is squeezed inside that little tube. It doesn't hurt?"

"Surprisingly, no. Although it is very uncomfortable when he tries to grow over a longer period of time."

Bobbie took her time caressing and kissing every inch of his body. By the time she finished, forcing her tongue into his mouth, he was trying not to squirm. His manhood pressed hard against the end of its prison, and a long strand of pre-cum dripped from it. She caught it on her hand and fed it to him.

"This really does drive you wild and fuck with your head... or heads... doesn't it?"

"You have no idea."

Bobbie grasped his chastity tube in her fist. "I have an inkling, because I really, really want your dick in me right now, and I cannot have it. So you have a lot to make up to me. I want one of your full body massages, then you are going to eat my pussy until I scream and beg you to stop, fucker."

She did a slow strip tease before him. Taking her polo shirt off revealed a light blue sports bra. Removing it freed her smallish, pert breasts with erect, upturned nipples. Sliding her cargo pants off revealed her very fit buttocks and thighs. Now all that was left were her lacy blue panties.

"Get down on your knees. Take off my panties with your teeth. It should be easy with my narrow hips... not like trying to get them past big-dick Barbie's fat ass."

When he was kneeling before her, she grabbed his head and forced his nose into the gussets of her panties. They were very damp and... aromatic. She was beyond excited. He made quick work of removing them, hungry for what they hid from him. Now he was rewarded with her plush auburn pubic hair, glistening with her arousal, and her plump, distended clitoris.

Two hours later, Bobbie fell back onto the bed, completely sated. She looked at Connor. His face looked like a glazed donut, pre-cum was leaking from his cage, his balls were swollen, and what little she could see of his penis was discolored and trying to burst through the vent holes. His entire body was trembling with need, and... the silly motherfucker was smiling!

Saturday afternoon Connor was supposed to spend time with his ex-wife. Their relationship had improved with counseling. But it was not the same as before her infidelity. He realized there would be no possibility of a slow reveal with her. She would know about his new attire as soon as she saw him.

Kathleen was relaxing on the couch watching TV when she received a text. *Here*

A flush of excitement went through her. In spite of everything that had happened, she still loved Connor, and wanted him back full time. She picked up the garage door opener and pressed it. She could very easily return to their former life, where she played the "little wifey"... but she had also discovered she enjoyed the hell out of being in charge when he visited. Her first rule had been that he could not wear clothing in "her" house. The simple power of the whole clothed female, nude male thing turned her on and made her feel good about herself.

The garage door went up and Connor backed his truck inside. He walked behind the truck and stripped naked. Knowing the interior door was locked, he threw his clothes into the cab, then ran to the front door. He rang the doorbell and waited patiently, not displaying his anxiety, wearing only the chastity device he could not remove.

Kathleen sat watching the television, waiting for a commercial to answer the door. It may seem callous, but it was Connor who had taught her to be selfish in this manner during counseling sessions. And through study material about female led relationships provided by Vivian, his therapist, such as "The Care and Feeding of the Non-Dominant Male."

Once a commercial came on, nearly five minutes later, she opened the front door to allow him entrance, of which he quickly took advantage.

As she regarded him, her eyes lit up, "Oh my, you've really gone and done it now, haven't you?"

He nodded.

Kathleen was very pleased. She had been teasing him during their sessions by fucking herself on a large dildo, as large as Mike, the man she had cheated with. Only on occasion had she actually had penetrative sex with Connor since they had gone to counseling sessions together. She had taken great advantage of his cunnilingus skills, but she had it in the back of her mind that she was saving intercourse for when they remarried. So the chastity device, to her, meant that scrawny little bitch he worked with couldn't have his dick either. Unless.

Disdainfully, "You did not give the keys to this contraption to your little work wife, did you?"

He shook his head, "No, ma'am."

She arched an eyebrow. Well?

"I gave them to Vivian to hold. She wants to talk to you about rules and guidelines."

She was less concerned about this development. Still. "Why her?"

"So you and Bobbie wouldn't be fighting over it... and because she is impartial."

"I suppose that makes sense. I gotta say, this is a turn-on, knowing you cannot even get hard or jack off. Go to the bedroom." She swatted him on the ass as he walked by. "Yummy."

Once in the bedroom, she asked him to disrobe her. He unbuttoned her blouse and removed her lacy bra, watching as her large, full breasts bounced free. Her large, eraser sized nipples were already erect.

He groaned as his own shaft tried in vain to become erect.

He removed her skirt, and took in her lacy black panties. Without being directed to do so, He knelt before her and pressed his face to her genitals, inhaling the intoxicating scent of her musk.

"Ooh, I like that." She felt herself moistening even more.

Connor grasped her panties in his teeth to pull them down. Bobbie had been right! It was much more difficult to pull the undergarment down past his ex-wife's big, beautifully shaped ass. He had to move around behind her and worked to pull them across her buttocks.

He had to force himself not to laugh, lest he had to explain. THAT would have pissed Kathleen off to no end. Even though his thoughts were how amazing it was to be attracted to Bobbie's little bubble butt, and Kathleen's expansive bottom equally.

For her part, Kathleen was incredibly aroused by his eagerness. She dropped back onto the bed and beckoned him to her bare, plump nether lips, which were already sopping wet.

"Make me cum, baby. Give me what you cannot have!" She used him all weekend. She gloried in the power of it all. She particularly enjoyed watching him become increasingly aroused, continuously building with no release possible. Secretly, she hoped to "break" Mister Stoic, to make him beg. He never did... yet.

Monday afternoon Kathleen found herself in Vivian's lobby, in response to a call that morning. They had "much to discuss."

Vivian opened the door from her office and beckoned Kathleen inside. Kathleen smiled in anticipation, until she entered the room to find Bobbie already there.

They had spoken kindly on the phone. But being in the same room with the "competition" was different. Tension filled the room.

Vivian tried to break the ice. "Well. Connor obviously made the correct decision for a key holder. Ladies, you don't have to like each other... but we are all going to have to work together. As long as you are still interested in helping Connor out."

That helped, strangely. Both of Connor's lovers loved him. It was not so much jealousy, but distrust that the other woman was "right" and "trustworthy" for Connor. At least that is what they told themselves.

Vivian explained that she did not want to be the person who chose winners and losers between them.

Bobbie asked, "That makes me happy. But how do you manage to control Connor's keys without choosing?"

Kathleen spoke, "You could just keep him for yourself and cut us both out."

Vivian smiled. "I can see where you could be concerned about that. I can assure you that will not happen."

Kathleen arched an eyebrow.

Vivian continued. "In the spirit of full disclosure, which I hope to receive from both of you in return, I AM using Connor's talents in cunnilingus to pay for my key holding services. But I will not be using his penis at all."

Another arched eyebrow.

"To set your mind at ease, I am a lesbian. I have never experienced a man's penis, and I do not desire to do so."

Kathleen softened. "Oh. Well, how does that work? If you aren't attracted to men?"

Vivian nodded with understanding. "A little background. I lost my life partner about three years ago. I honestly thought my sex life was over. It has been a difficult three years. Then the two of you began telling me about Connor's... umm... talents. The key holding thing opened up an opportunity. My lord, he really does eat pussy like a girl, doesn't he?"

They all laughed heartily.

"Anyway. He does not know it yet, but Connor has been therapeutic for me. I have begun dating again because of his... work."

Bobbie smiled, "That is great!"

Kathleen agreed. "So, what is the plan?"

Vivian smiled patiently. This one was all business. "Well, I do have a plan. And I need your buy-in. Connor wants random denial, to be pushed to his limits. As I said, I do not want to intentionally choose between you two."

She withdrew two nice boxes from her desk drawer and opened them. One contained padlocks, the other keys.

"Here is my plan, if you agree. I have purchased twelve small padlocks. Each came with two keys. I have one full set of keys locked up here. I have had the identifying numbers filed off of the locks and keys."

She paused for effect.

"Connor's chastity device will be secured by TWO padlocks. Each Tuesday during his session, I will replace the padlocks randomly, after shaking the box of locks up."

"Each Monday, I will mail both of you two keys. I won't even know whether the keys I send you will unlock anything. If they don't, we start again the next week. If they do unlock both locks, whoever frees the willy, gets it for that week. During his next session, I will lock him up again."

Bobbie gasped. "It could take months before he got lucky enough to have them all match!"

Vivian nodded. "Or one week. No way to know."

Kathleen chuckled, "It's genius. And evil."

Bobbie added, "I love it. I'm in."

Kathleen agreed, "Me too."

Vivian added, "Just so you know, he will be let out during our sessions. If you remember from care and feeding... if he stays in the cage too long without getting erections, he'll shrink. I don't think either of you want that."

They spoke together, "Hell no!"

"Our sessions will last about an hour and a half. 45 minutes of counseling, and 45 minutes of cunnilingus... then I'll ice him down and lock him back up until one of you lets him cum... assuming you choose to do so. I'll also have him clean and shave himself under supervision."

Vivian seemed to think of something else. "Also, if you find it enjoyable at any time, either one of you are free to milk him."

Bobbie asked, "Milk him?"

"Yes. It's in that manual, or you can find instructions online. Prostate milking, or massage. You use your finger, or a wand made for the task, and massage his prostate. It will feel good, but it will not result in orgasm. It will, however, result in the built-up semen being released. I understand it is quite frustrating for the man, because he can feel the semen pouring out, but gets no relief."

Bobbie looked shocked. "That is diabolical. I can't wait to try it."

Kathleen tittered conspiratorially, "Poor bastard."

They were all agreed on the care of their mutual lover and victim. Bobbie and Kathleen still did not trust one another, but the system seemed fair.